54447-84-6Relevant articles and documents
Cyclic oligoribonucleotides (RNA) by solid-phase synthesis
Micura, Ronald
, p. 2077 - 2082 (1999)
A novel solid-phase synthesis of small-to medium-sized cyclic RNA oligonucleotides is presented. A major advantage of the approach is the lack of restrictions on the sequence variety with respect to the four standard bases adenine, cytosine, guanine, and uracil. This has been demonstrated for cycles containing 2 to 21 nucleotide units. The approach allows fully automated assembly, and is related to a procedure known for the preparation of cyclic oligonucleotides in the DNA series (E. Alazzouzi, N. Escaja, A. Grandas, E. Pedroso, Angew. Chem. 1997, 109, 1564-1567; Angew. Chem. Int. Ed. Engl. 1997, 36, 1506-1508). It combines standard phosphoramidite chemistry for chain elongation and standard phosphotriester chemistry for ring closure. A key aspect of the method is use of the novel 2′-O-triisopropylsilyloxymethyl (TOM) protected RNA phosphoramidites (X. Wu, S. Pitsch, Nucleic Acids Res. 1998, 26, 4315-4323) instead of the classic tert-butyldimethyl silyl (TBDMS) protected amidites. Furthermore, the design of the final cleavage step is selective only for correctly cyclized oligoribonucleotides. This results, after deprotection, in HPLC profiles in which the crude oligonucleotide is represented by the major peak with typically more than 80% of the integrated area. The ring closure itself proceeds with an average yield of 15%.
Identification of bromophenol thiohydantoin as an inhibitor of DisA, a c-di-AMP synthase, from a 1000 compound library, using the coralyne assay
Zheng, Yue,Zhou, Jie,Sayre, David A.,Sintim, Herman O.
, p. 11234 - 11237 (2014)
c-di-AMP is an important bacterial second messenger found in Gram-positive and mycobacteria. c-di-AMP regulates myriads of processes in bacteria as well as immune response in higher organisms so interest in small molecules that would attenuate the activity of c-di-AMP metabolism enzymes is high. Herein, we report the first small molecule inhibitor of a c-di-AMP synthase, DisA, using a coralyne-based assay.
Highly Efficient Cyclic Dinucleotide Based Artificial Metalloribozymes for Enantioselective Friedel–Crafts Reactions in Water
Wang, Changhao,Hao, Min,Qi, Qianqian,Dang, Jingshuang,Dong, Xingchen,Lv, Shuting,Xiong, Ling,Gao, Huanhuan,Jia, Guoqing,Chen, Yashao,Hartig, J?rg S.,Li, Can
supporting information, p. 3444 - 3449 (2020/02/04)
The diverse secondary structures of nucleic acids are emerging as attractive chiral scaffolds to construct artificial metalloenzymes (ArMs) for enantioselective catalysis. DNA-based ArMs containing duplex and G-quadruplex scaffolds have been widely investigated, yet RNA-based ArMs are scarce. Here we report that a cyclic dinucleotide of c-di-AMP and Cu2+ ions assemble into an artificial metalloribozyme (c-di-AMP?Cu2+) that enables catalysis of enantioselective Friedel–Crafts reactions in aqueous media with high reactivity and excellent enantioselectivity of up to 97 % ee. The assembly of c-di-AMP?Cu2+ gives rise to a 20-fold rate acceleration compared to Cu2+ ions. Based on various biophysical techniques and density function theory (DFT) calculations, a fine coordination structure of c-di-AMP?Cu2+ metalloribozyme is suggested in which two c-di-AMP form a dimer scaffold and the Cu2+ ion is located in the center of an adenine-adenine plane through binding to two N7 nitrogen atoms and one phosphate oxygen atom.
